


Untitled Crossdressing Fic

by whispered_story



Series: Lingerie Verse [1]
Category: Supernatural
Genre: Crossdressing, Dean in Lingerie, Halloween, Holidays, M/M, Stanford Era
Language: English
Status: Completed
Published: 2015-09-09
Updated: 2015-09-09
Packaged: 2018-04-19 22:03:44
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,957
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4762682
Author URL: https://archiveofourown.org/users/whispered_story/pseuds/whispered_story
Summary: <blockquote class="userstuff">
              <p>Dean visits Sam at Stanford. [reposted, first posted on livejournal 9/4/2012]</p>
            </blockquote>





	Untitled Crossdressing Fic

There are some things that Sam and Dean don't talk about.

Like, their mom's death. Or that they've been sleeping together since Sam left college and started hunting with Dean again. Or Jessica. Or that fateful night when Dean was nineteen and got so drunk he puked on Sam and then told him that, when he looked at Sam, he felt whole -- Dean's still pretending that night actually never happened and Sam lets him.

But what they definitely don't talk about is the one time Dean came to visit Sam at Stanford during his sophomore year. 

It doesn't keep Sam from remembering that night -- and every goddamn, tiny detail about.

+

"Dean?" Sam asked into the phone when he picked up, both surprised and disbelieving.

"Hey, Sammy," Dean said. Casually. As if it hadn't been over a year since they last talked to each other.

"Hey," Sam whispered, sinking down onto his bed. He drew his feet up onto the mattress, curled his arm around his legs, and rested his cheek on his knees. "What's up?"

"Nothing," Dean said. "I'm in the area. I was wondering if it was okay if I dropped by?"

"Here?" Sam asked.

"Well, yeah," Dean replied. "Wasn't gonna call you and ask to drop by somewhere else."

"When?"

"Tonight," Dean replied.

Sam looked around, half expecting Dean to appear in the middle of his dorm room out of nowhere, with a cocky grin and smelling of leather and gun powder.

"It's Halloween," Sam replied lamely. "I, uh, I'm going to this party."

"I could come," Dean offered.

"You'd...you'd have to wear a costume," Sam said, and he didn't really know why he was trying to talk Dean out of coming to Stanford. To Sam. Since he got here, Sam had thought about this -- he would walk around campus, imagining showing Dean around, or he'd meet friends at some tiny diner or café that sold cheap, greasy food and he'd think about nothing but how much Dean would like it.

"I'll find something to wear. Don't worry, I won't embarrass you in front of your little college friends."

Sam didn't say that he really wasn't worried about that. What he _was_ worried about was that, once he saw Dean again, he wouldn't want to let him go. 

"Okay," Sam said. "Yeah, okay. I...I'd like it if you came."

+

Sam was pacing in his room, glancing at the alarm clock next to his bed every few seconds. Dean should be there any minute, and Sam's stomach was in knots. It had been so long since he'd seen Dean, and every fiber of his being missed Dean, longed for him.

Sam took a deep breath and tried to calm himself down, telling himself it wasn't a big deal. He caught sight of himself in the mirror -- pointy vampire teeth, pale skin, a long dark cape -- and thought to himself that, maybe, he could pretend the tension in his shoulders and his drawn expression were a character choice. It was, in no way, due to the fact that he was freaking out about Dean visiting him.

A knock on the door startled Sam, and he smoothed down his dark shirt before stepping up to the door and pulling it open.

There was a girl on the other side, and Sam was about to tell her his roommate had already left with some other girl -- it wouldn't have been the first time the guy had several dates lined up for one night and then left Sam to deal with it -- when he did a double take. The girl was tall, with green eyes, freckles, and a cocky grin.

"Dean?" Sam asked, gaping.

"Hey there, Dracula," Dean drawled out, his usually low voice a lot higher and kind of breathy.

"What the--," Sam started.

Dean laughed. "Turns out when you need a costume for a Halloween party a few hours before said party begins, you can't be too picky," he said. "Luckily, I apparently make one hot chick."

Sam couldn't really argue with that, because Dean actually looked better than most of girls Sam knew. He just stepped aside and hoped the pale make-up a friend's girlfriend had done for him would hide his blush.

Dean stepped inside and turned in a slow circle in the middle of the room. "So this is where you live?" he asked.

He was wearing fishnet stockings, a short black skirt and a chunky, dark gray sweater that slid off his left shoulder. His short hair was replaced by a dirty, blond wig, hair falling down to his shoulder. He looked...like a real girl. 

"Do you have boobs?" Sam asked, ignoring Dean's question, because the heavy sweater did nothing to hide the soft, small curves of what looked like breasts.

Dean's lips quirked into a smile. "Sammy, my face is up here," he said loftily, pointing to his face, and Sam flushed.

"Shut up," Sam muttered. 

Dean laughed. "They look real, right?" he asked gleefully. "It's really just a padded bra and tissues, but I think I did a good job."

"Uh, yeah," Sam answered, still not able to take his eyes off his brother. "It looks...good."

"I know," Dean replied. "Figured I would pass as a girl dressed up as an arsty, emo chick at that party of yours."

"Uh, okay? I thought you're, you know, trying to be a guy dressed as a chick?"

"Hell no," Dean said with a laugh. "It'll be a lot more fun if all the college boys think I'm a girl."

"You want college guys to hit on you?"

Dean batted his eyelashes. "Why, yes, Sammy. And then I'll tell everyone that I came with the tall drink of water pretending to be Dracula for the night and everyone will think you're cool for scoring a hot girl," he said, then paused. "Unless you have a girlfriend. Then I probably shouldn't say I'm your date."

"I don't," Sam said softly. "So, uh, you want to pretend to be my girlfriend?"

Dean laughed again, and he sounded a lot more carefree than Sam remembered. "Nah, just your hook-up or else you might have some explaining to do. Come on, it'll make that stupid party a lot more entertaining," he said. "What d'you say? Wanna see if we can pull this off?"

Sam knew he should say no. Nip the idea in the bud, because none of Dean's ideas were ever good. They were reckless and insane and caused them more trouble than it was worth.

"Okay," Sam agreed.

+

"Some guy grabbed my ass," Dean said cheerfully, and handed Sam his drink. Whatever was in the red cup was a murky, brown color and did not at all look like something Sam wanted to drink.

"And you enjoyed it?" Sam asked doubtfully.

Dean grinned. "Hell, yeah. I slapped him and everyone was totally on my side. It was awesome."

Sam sighed. "Of course."

"Aw, Sam. Don't look so down. You're not having fun?" Dean asked, and he batted his ridiculous eyelashes at him. Sam had been trying to figure out if they were fake or actually Dean's all evening.

"It's okay," Sam said with a shrug.

"Don't--" Dean started, then stopped and made a face, peering at something over Sam's shoulder. "Ugh. It's gropey guy."

"Gropey guy?" Sam echoed.

"Shut up. The guy groped me. The name makes sense," Dean argued. "And now he's watching us all creepily."

"Guess that makes him creepy gropey guy," Sam said.

Dean glared at him. "Seriously, this isn't funny. I feel violated," he complained. "Just because I'm smoking hot, doesn't mean he's allowed to get disrespectful. Plus, I'm obviously here with you."

"We're standing side by side, talking. That doesn't exactly scream 'we came with each other,’" Sam pointed out.

Dean's lips twitched into a smile. "Ha. Came with each other," he repeated, wiggling his eyebrows.

Sam groaned. "Dean."

"You need to loosen up."

"Says the guy who is all worried because someone is hitting on him."

"Not just someone," Dean said. "The guy gives me the creeps."

Sam sighed. "You wanna leave?" he offered.

Dean rolled his eyes. "No. I want you to do something about it," he replied. "Obviously, the guy doesn't take no for an answer, so maybe words aren't enough."

"So what do you want me to do? I'm not starting a fist fight with some guy to protect your honor," Sam said. "You can kick his ass yourself."

"I'm a _lady_ , Sammy," Dean replied sweetly. "And you don't need to kick his ass. Just -- be a little bit more possessive, would you? I'm your date, remember?"

"Possessive?" Sam echoed.

Dean sighed. He grabbed Sam's free hand and tugged it around him, making Sam's hand rest low on his hips. Sam most definitely did not squeak.

"You want to stop some guy from groping you by making me grope you instead?" he asked, startled.

Dean rolled his eyes. "Why not? You're -- you. Why would I care if your hands are on me?" he said with a shrug. "No, come one, man up and show that guy that he isn't allowed to hit on what's yours."

"You're not mine."

"It's called pretending, asshole," Dean muttered. He shifted closer, pressing his body against Sam and Sam involuntarily tightened his arm around him. It felt...nice. Dean was warm and firm, molding against him perfectly.

"See? It's not that hard, right?" Dean asked and he sounded oddly breathless.

"Uh, no. Not hard at all," Sam replied and willed his cock not to betray him.

Dean licked his lower lip, glancing to the left at where Sam assumed the guy was. "Maybe," Dean said. "Uh, maybe you should kiss me. Just, you know, to really get the message across."

"I...yeah. Maybe," Sam answered, unable to remember why this was an epically bad idea.

He ducked his head down and Dean leaned up, meeting him halfway. Dean's lips tasted like strawberry lip-gloss, sticky and sweet, and if it wasn't for the fact that Sam wasn't able to form a single coherent thought, he'd probably have been impressed by how committed Dean was to his Halloween costume. But all Sam could do was moan into the kiss and pull Dean closer, his hand cupping the perfect swell of Dean's ass.

Distinctly he thought he heard someone catcalling, but he was too focused on the feel of Dean's body against his. He tried to hitch Dean a little higher and Dean made a strained noise, lifting up. Sam fleetingly thought Dean must be standing on his tiptoes, but then he nudged his thigh between Dean's legs and _holy shit_ , that was Dean's cock pressing against his leg and he didn't know what Dean was doing as long as Sam got to feel him like that.

"We should get out of here," Dean murmured when they broke the kiss.

"Yeah," Sam panted. "Yeah, we should."

+

The next morning, Sam woke up alone in his too small bed.

There was dried come on his stomach -- _Dean's_ , his mind supplied -- and a used condom lying next to the bed. 

Dean was gone.

All he'd left was a black, silky bra hanging over the end of Sam's bed, crumbled tissues lying on the floor beneath. 

Sam lay back in his bed, closed his eyes, and pretended his eyes didn't sting as he thought about last night. About the way Dean had kissed him, needy and eagerly, and the way he'd felt when Sam slid into him. About the choked off moans Sam had drawn from Dean's lips with each thrust of his hips and the way Dean's fingers had been digging into his arms.

It was the last time Sam dressed up for Halloween.


End file.
